What Is Nitroacetanilide?
Nitroacetanilide is a nitro derivative of acetanilide with the chemical formula C8H8N2O3.
There are three positional isomers, 2-nitroacetanilide (o-nitroacetanilide), 3-nitroacetanilide (m-nitroacetanilide), and 4-nitroacetanilide (p-nitroacetanilide), depending on the substitution position of the nitro group.
The molecular weight is 180.16, and all three isomers exist in a solid state at room temperature.
Uses of Nitroacetanilide
The main uses of nitroacetanilide are as a raw material for organic synthesis and as an intermediate in organic synthesis.
For example, in the synthesis of 4-nitroaniline, the amino group of aniline is protected to make acetanilide, and then 4-nitroacetanilide is used as an intermediate in the nitration reaction. This is because direct nitration of aniline leads to decomposition by oxidation and orientation changes due to the formation of anilinium salts.
4-nitroaniline is a useful compound with a variety of industrial applications, such as an intermediate in the synthesis of dyes and pharmaceuticals, an antioxidant, and an anti-gumming agent in gasoline.
Properties of Nitroacetanilide
1. 2-Nitroacetanilide
2-nitroacetanilide (o-nitroacetanilide) has a melting point of 93°C and is a pale yellow or brown crystalline powder at room temperature. The CAS registration number is 552-32-9.
The CAS registration number is 552-32-9. It should be kept away from high temperatures and direct sunlight during storage, as it may be altered by light. It also reacts with strong oxidizing agents, and therefore, mixing should be avoided.
2. 3-Nitroacetanilide
3-nitroacetanilide (m-nitroacetanilide) has a nitro group attached at the meta (3-position) from the amide group. The melting point is 151-154°C. It is a light yellow to yellowish brown crystalline powder at room temperature.
The CAS registration number is 122-28-1. It should be kept away from high temperatures and direct sunlight during storage, as it can be altered by light. It also reacts with strong oxidizing agents, and therefore, mixing should be avoided.
3. 4-Nitroacetanilide
4-Nitroacetanilide (p-nitroacetanilide) has a nitro group attached at the para (4-position) from the amide group. It is a yellow to yellowish-brown crystalline powder with a melting point of 213-216℃. It is soluble in ethanol and acetone, but insoluble in water.
The CAS registration number is 104-04-1. It should be kept away from high temperatures and direct sunlight during storage, as it may be altered by light. It also reacts with strong oxidizing agents, and therefore, mixing should be avoided.
Types of Nitroacetanilide
Nitroacetanilide, as mentioned above, has three different positional isomers, all of which are commercially available as reagent products for research and development. The types of volumes include 25g, 100g, etc. They are sold as reagent products that can be handled at room temperature.
Other related derivatives marketed include 2′-methyl-4′-nitroacetanilide, 4′-fluoro-2′-nitroacetanilide, and 4-acetoxy-1-acetylamino-2-nitrobenzene.
Other Information on Nitroacetanilide
Synthesis of Nitroacetanilide
2-nitroacetanilide and 4-nitroacetanilide can be obtained by the following process.
- Synthesis of acetanilide from aniline (acetylation reaction of the amino group of aniline)
- Nitration of acetanilide with mixed acids (aromatic nucleophilic substitution reaction)
- Purification of the mixture of 2-Nitroacetanilide and 4-Nitroacetanilide
The aromatic nucleophilic substitution reaction in 2 is ortho-para oriented, especially favoring the para position. Therefore, this reaction produces 4-nitroacetanilide as the main product and 2-nitroacetanilide as a byproduct; to synthesize 3-nitroacetanilide, another synthetic route is used.